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Book Online or call HomeAway Booking Assistance +44-800-085-3815
Book Online or call HomeAway Booking Assistance +44-800-085-3815

Very special, 2016 restoration, Immaculate Highland Lake direct-waterfront

Bedrooms 3
Space 1,300 sq ft
Property type house
Minimum Stay 2 - 7 nights


About the property

Wonderful family vacation house. Nice swimming area, large deck, dockage

RATE NOTE: Email for special rates on off-season visits for more that 3 days.

If you are aesthetically minded, if you are looking for something particularly charming and special, you will love this cottage. If you are seeking a very nice spot on the lake, you will love this property. Canoe, Kayak, Sunfish Sailboat, and more to enjoy.

If you have rented cottages before, you know that location on the lake makes a difference. Our cottage is located on the favored east side of the lake, with best sunshine. It is located away from the boat traffic and boat wake waves, on a quiet cove open to the largest of the lakes bays. Nice swimming area for kids. Its has the important things experienced visitors recognize.

It is a Victorian beauty, but fully restored in 2016 to high standards. Toasty warm in winter with lower level radiant heated floor, air conditioned for summer.

Fully equipped kitchen, open-concept. We re-purposed original and vintage materials for this loved Victorian era cottage during our restoration. Every window and door has a story. Just ask us!

Easy to use fireplace. Great for crisp mornings.

Bedrooms include: one queen, one full and 2 bunks. Wake up in the queen and full bedrooms to sunrise on the lake. Spectacular views. Also upstairs, is a comfortable reading area and desk, a full bathroom with a 2 person, fully tiled shower, while the downstairs bath boasts a sparkling, new claw foot soaking tub.

Downstairs, you will find a fully equipped kitchen, full-sized fridge, dual-fuel stove (gas stove top/electric oven), dishwasher and apron farm sink. Guests can dine on the old world dining table and Hitchcock chairs made locally, or at the kitchen peninsula. We have an open concept kitchen/dining/living room area which opens, through french doors, onto a large deck, just steps from the lake front. Enjoy the gas grill and picnic table for afternoon BBQs or glowing white lights and sunsets for a lovely evening dinner party.

Bring your boat or jetski and tie up at our lakefront dock. This lake is great for swimming, boating, water-skiing and fishing. Private lawn and water front. Sunny side of the lake. The cottage is close to 'the Secret Spot,' (shallow area great for small children to play in the water). We live next door to the cottage. Our boat is parked on the south side of the dock in front of our place, your boat, if you bring one, is docked on the right north side directly in front of your cottage.

Our area offers wonderful restaurants and grocers using locally produced food, Farmer's Markets (don't miss Litchfield's Saturday Farmer's Market!), the Gilson Cinema/Cafe, Antiquing, nearby fly-fishing, hiking, and biking. Stop in at a local farm for just picked corn or tomatoes, or an after dinner ice-cream cone.

For anyone up for a Berkshires experience, we are less than a one hour, country drive from Tanglewood, Shakespeare and Co., Stockbridge, Great Barrington, Lenox, and the Outlets at Lenox.

During the summer, we request a minimum 7 day booking, Saturday to Saturday. Also, we cannot accommodate pets, due to potential allergies of renters. However, there is a highly respected kennel close to the other side of the lake.

Of course, it's great in the summer, but fall and winter offer their own special activities. Fall leaves, apple picking, hay rides and pumpkin patches in the country. Winter snow, skiing, flannel sheets and cozy fires. Our cottage can comfortably accommodate all seasons!

More Details

Member since: 2016
Premier Partner

This partner has demonstrated and is committed to fast response times, the best rates, and a great guest experience.

Speaks English, Spanish
Response time:
Within a few hours
Response rate:
Calendar last updated:
17 August, 2018


Long time lake resident, long ago it won my heart. We made a lot of memories over the years here. When the time came to rebuild the cottage, we wanted to keep it true to the early 1900's cottage it had always been. It has all the modern conveniences now, but despite this, I hope you agree we maintained its authentic charm. It still feels like the cottage our family grew up in over those many golden summers, long to be remembered. We welcome others now to make special memories too. purchased this house in 1971

Why chose Winchester

Great property and location on the lake.


Accommodation and facilities for this holiday house in Winchester in Litchfield County

Property Type:
  • house
  • Self-catering
Floor Area:
  • 1300 sq ft
House Rules:
  • Check-in: 15:00 / Check-out: 11:00
  • Max. occupancy: 7
  • Minimum Age Limit for Renters ...
  • children welcome ...
  • pets not allowed
  • non smoking only
Location Type:
  • Lakefront ...
  • Adventure
  • Away From It All
  • Family
  • Romantic
  • Air Conditioning ...
  • Clothes Dryer
  • Fireplace
  • Heating ...
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking ...
  • Telephone
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Hob ...
  • Toaster
  • Dining Area
  • seating for 7 people
  • 2 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
  • Bathroom on the bedroom level has a shower. Bathroom on the lower level has a soaking tub.
  • 3 Bedrooms, Sleeps 7
  • Books
  • Games
  • Satellite / Cable
  • Television ...
  • Terrace ...
  • Kayak / Canoe
  • Garden
  • Barbecue ...
  • Long-term Renters Welcome
  • autumn foliage
Leisure Activities:
  • antique hunting
  • bird watching
  • photography
  • scenic drives
  • sledding
  • walking
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness centre
  • groceries
  • hospital
  • laundrette - serviced
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • fishing
  • freshwater fishing
  • golf
  • hiking
  • ice skating
  • jet skiing
  • mountain biking
  • sailing
  • swimming
  • water skiing
  • water tubing


Wonderful! 4.9/5 -
(15 traveller reviews)

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Very special, 2016 restoration, Immaculate Highland Lake direct-waterfront
average rating of 4.9333334 based on 15 reviews

Wonderful lake getaway

  • 5 of 5

We had a terrific week on HIghland Lake. The house is lovely, just right for our family (including our 5 and 7 year old daughters). Quaint and charming bedrooms, updated and clean bathrooms, and small but great kitchen. The deck is outstanding, like an additional room outdoors! The lake is perfect, great time canoeing and kayaking. Fun swimming off of the dock for hours a day. The Owner was so nice, very available, but not at all intrusive. All in all, an excellent place to visit, we highly recommend it!!

  • Review Submitted: 26-Jul-2018
  • Date of Stay: July 2018
  • Source: HomeAway
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Great location, cottage, and owner!

  • 5 of 5

John was great! We were quite a bit late on our first night, and he offered to let us stay an extra on the back end. Unfortunately we weren't able to take advantage of his incredible hospitality, as we had flights out to catch, but it was extremely generous of him.

Additionally, the accommodations were tremendous. The cottage was incredible, and so charming. There was a bottle of wine and some snacks, from John, on the counter when we got there and the fireplace was already warming the house. The deck was incredible, and the view was so calming and peaceful. We grilled out both nights, and had an amazing time. The beds were so comfortable, and we will hopefully be coming back again.

  • Review Submitted: 22-May-2018
  • Date of Stay: May 2018
  • Source: VRBO, from HomeAway
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Idilic lake front setting with Kayaks

  • 5 of 5

This was the most relaxing vacation we have had in years. Stunning setting. Very confortable and pretty, renovated cottage. Cottage was immaculate, well equipped and well located.

The owners could not have been kinder, providing enough goodies to get us started on the day we arrived ( lovely touch). John graciously allowed us use of his boats on the lake and we enjoyed kayaking and having mini picnics with our 6 year old who just loved playing on the water - he woke up singing and went to bed singing. The perfect family vacation.

Stunning part of CT and although in the country was only a 5 min drive into town - best of both worlds.

Will be back! Thanks John for a vacation we will always remember with much fondness! Thanks for your time that you gave to us too.

  • Review Submitted: 16-Oct-2017
  • Date of Stay: October 2017
  • Source: VRBO, from HomeAway
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We had a fantastic early fall visit on our favorite New England lake!

  • 5 of 5

This was our first time staying here and it was perfect for my mom, sister and I and our two young daughters. The place is amazingly renovated with such attention to detail. The deck was beautiful and is cut around the trunk of a large maple tree. We used the propane grill on the deck one day and ate lunch at the picnic table for a memorable family meal. The kitchen was perfect and we also made use of the gas fireplace. Internet and TV setup were great with no issues. No cell reception though, which we expected and was fine. WiFi was sufficient for communicating with most people. There is no insulation between the first and second floors (which I thought was fine since you get to see the beautiful wood of the floor on the bottom as well as the top), but this could be a problem for light sleepers tying to sleep late with others up and about making noise. I love the lake off-season and hope to brave it during winter someday! Long live Highland Lake! Jack was a great host and fit in a last minute boat ride for us - which was magical and joyous. The first motor boat ride for our little girls! Thank you for a great stay, Jack!

  • Review Submitted: 08-Oct-2017
  • Date of Stay: September 2017
  • Source: HomeAway
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Bristol, CT, USA

Fisherman's Dream!

  • 5 of 5

My husband and I stayed from Sept. 17 to Sept. 23. Had a nice relaxing time enjoying the peacefulness of Highland Lake in the fall. Enjoyed fishing whenever we wanted. Lake house was very close to all the stores you might need to go to. Can't SAY enough about the OWNER--John was very helpful (above and beyond). Definitely would stay here again!

  • Review Submitted: 23-Sep-2017
  • Date of Stay: September 2017
  • Source: VRBO, from HomeAway
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Lovely house and beautiful place!

  • 4 of 5

We had a nice stay in this well equipped house. Because af the thin wooden walls it was a bit noisy inside, but i think that 's due to the way it is build.

  • Review Submitted: 18-Sep-2017
  • Date of Stay: September 2017
  • Source: HomeAway
Owner's Response: Hi Rudi, Thank you for the card and kind gift, that was a nice surprise. Regarding sound inside the cottage, you are the second person to report that to us. The cottage is all wood floors, so that has some effect on sound. But what we are concluding in this first year of renting the cottage is that our decision to leave the lower level ceiling as the open beams, causes more sound than we would like to travel upstairs through the ceiling to the upper level. We really liked the look of the original beamed ceiling, but I think I may need to fill in between the ceiling beams with wood and soundproofing to end the sound transfer through the floor. All the interior walls are actually full 4.5 inch thickness, and solidly built. In addition there is dense cotton soundproofing filling the inside of all the interior walls to prevent sounds being heard between rooms. The exterior walls are all six 6.5 inches thick, have full insulation, and windows are double and triple glass. Looks like our next project is to have the carpenter to soundproof the ceiling between the two levels. Thanks, John
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Nearest Airport
35 Miles
Nearest Ferry
60 Miles
Nearest Train
25 Miles
Car: necessary


Prices & Availability

Ask Owner a Question

Additional pricing information

Cleaning Fee £77.25
Refundable Damage Deposit £154.5

In off-peak months (September through May), feel welcome to inquire about short term lease. The home is state of the art, an ideal executive rental for a period of months, in a remarkable setting, great year round. In Summer months, rental week runs from Saturday to Saturday.

Owner's Cancellation Policy

  • 100% refund for cancellations more than 60 days before check-in date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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